Z. Cimerman et al., THE STRUCTURE AND TAUTOMERIC PROPERTIES OF 2-(3-PYRIDYLMETHYLIMINOMETHYL)PHENOL, Journal of molecular structure, 323, 1994, pp. 7-14
The structure and properties of 2-(3-pyridylmethyliminomethyl)phenol h
ave been determined by X-ray crystallography, NMR, UV and IR spectrosc
opy and compared with the characteristics of the Schiff bases derived
from salicylaldehyde and aminopyridines. Crystal data: C13H12N2O, M(r)
= 212.250, monoclinic, space group P2(1)/n, a = 10.49(1) angstrom, b
= 9.002(4) angstrom, c = 12.42(1) angstrom, beta = 109.10(4)-degrees,
V = 1109(2) angstrom, Z = 4, D(x) = 1.271 g cm-3, MoKalpha (lambda = 0
.71073 angstrom), mu = 0.8 cm-1, F(000) = 448, T = 297 K, R = 0.049, R
(W) = 0.053 for 886 reflections with I > 2sigma(I). Bond distances and
bond angles are similar to those of 2-(pyridyliminomethyl)phenols. In
the title molecule the dihedral angle between the pyridine and benzen
e least-squares planes is 89.9(2)-degrees. There is an intramolecular
O1-H ... N1 hydrogen bond of 2.572(5) angstrom. In solutions of polar
solvents tautomeric interconversion of the Schiff base into the ketoam
ine is observed. Corresponding equilibrium constants are estimated in
a variety of solvents on the basis of UV spectral data.